


It's a match

by NotfunnyDean (IronEyes)



Category: Supernatural
Genre: <3, Angst and Fluff, Angst with a Happy Ending, Bottom Dean Winchester, Crying Dean Winchester, Cute Dean, Dean Winchester Feels, Dean is an Idiot, Dean tries to matchmake Cas and Sam, First Kiss, Fluff, Getting Together, M/M, Making Out, Mutual Masturbation, NSFW Art, Online Dating, Polyamory, Sexting, Soft Dean, anonymous chatting, but it takes them a while, cute nicknames, dating app, dating apps, drama and fluff, implied - Freeform
Language: English
Status: Completed
Published: 2020-10-14
Updated: 2020-10-14
Packaged: 2021-03-07 23:27:55
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 10,242
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26995912
Author URL: https://archiveofourown.org/users/IronEyes/pseuds/NotfunnyDean
Summary: When Dean suffers from his feelings for his brother and the angel Castiel, he decides to do something about it. He tries to matchmake them on a dating app. He gets the app himself, only to look if those two really get it on of course. But somehow he starts flirting with them anonymously and falls even harder for them. Is there a way out without hurting anyone?
Relationships: Castiel/Dean Winchester/Sam Winchester
Comments: 8
Kudos: 64
Collections: Wincest Big Bang 2020





	It's a match

**Author's Note:**

> It's me again! :) 
> 
> So this is for the Wincest Bang, but somehow it turned to Wincestiel along the way <3 It was a lot of fun to write and the challenge was great.
> 
> I also want to thank my wonderful Artist [LeafZelindor](https://archiveofourown.org/users/LeafZelindor/pseuds/LeafZelindor) for the art to this story. Really it's amazing!!! Even got my first peen <3 Love you Leaf.
> 
> And of course my beta Reader [Cas!](https://archiveofourown.org/users/An_Angel_A_Muse) You're the best!
> 
> Aaand now: Here you can find the [Art Masterpost](https://leafzelindor.tumblr.com/post/631973214658215936/) ! Go check it out!! It's super cute and fantastic!
> 
> Have fun! x

Dean sighs into his coffee mug. It has been quiet the last days in the bunker, even though he is not alone. Of course Sammy is here, but also Castiel spends most of his time with them lately. Still Dean feels restless. 

Not for a hunt.

Dean isn’t sure what he is looking for to be honest, but it makes him crazy. Just as he wants to go up to get a refill for his coffee, Sam walks into the kitchen. Seems like he just woke up, because he yawns and then stretches in the doorway. 

Dean licks his lips, when he sees Sam’s stomach where the shirt rides up. And that’s when his stupid brain remembers. He is restless because of Sam. Because of his stupid feelings for his own brother.

“Good morning.” Sam says and walks over to get himself a coffee. Dean doesn’t even answer, but holds up his mug in greeting. Sam looks happy lately, Dean knows he is glad that there aren’t any urgent hunts.

While Dean loves to hunt, he has to admit how nice it is to spend time with Sam and Castiel not covered in blood and guts. Just watching movies or sometimes playing games. 

“Are you okay?” Sam asks and he seems a bit worried, when Dean is still staring. Dean hastily looks down into his own mug.

“Sure.”

Not his best lie, but also not the worst. Just as Sam wants to answer, Castiel walks into the kitchen. He is not wearing his trenchcoat after Dean had told him for two full weeks to lose that thing when they are at _home_.

He looks good in just a shirt and jeans. Dean groans quietly. Sam is not really the only problem here. Dean had fought his feelings his whole life, that doesn’t mean he doesn’t know that he is falling for Castiel too. 

His brother and an angel? Yeah no surprise he was in hell for forty years. 

He deserves worse actually.

“I got us the seeds for the flowers.” Castiel says, acknowledging Dean only with a short nod, before he goes over to Sam to show him. He has several packages and they are all in a different color. 

Dean squints.

“Flowers?” Dean wants to know and that gets him some attention. Sam’s bitchface number 67 looks still the same and Castiel tilts his head, the frown matching Sam’s face though. Dean swallows.

“Yes.”

“We want to have a small garden and while I got us some herbals and vegetables, Cas also mentioned how some flowers would be good for bees and other insects.” Sam explains and Dean nods meekly.

He hadn’t mean to judge. 

“That sounds… uh cool.” Dean gets out but Sam has his back already back to him, while Castiel explains which kind of flowers would attract the most bees. Dean sighs quietly. 

Sometimes he likes to see how Sam and Castiel interact. They grew a lot closer over the last years and in the last weeks you don’t meet them a lot without the other.

Sometimes though Dean gets jealous and today he can’t hide it very well. That is _his_ brother and _he_ has a profound bond with the angel! Why are they never inviting him to things anymore?

“We could start right now? I got the shovel and everything outside already.” Sam says and Castiel takes his seeds and some more coffee with them. Dean watches after them, looking down at his own plate.

He is not even interested in the bacon anymore.

Sure he knows how wrong it is to be in love with his own brother and also an angel. He still wishes he could… he could ask them out. No, he’d like it even more if they’d ask him out, because Dean may be brave in a lot of situations, but this is not one of them.

He knows that this will stay a dream forever though.

Dean looks back to the door. Sam and Castiel would never want someone like him. He doesn’t care about flowers or bees or salad and morning walks and whatever those two do all day and…

 _Oh_.

Sam and Castiel.

Castiel _and_ Sam.

Of course.

They would be the perfect match, how did Dean never see that before. Castiel would love to join Sam for the morning jog. They are already planting flowers together and they surely both love to sit in their library and read together. 

Dean’s heart aches at the thought. Castiel and Sam would be good for each other, unlike Dean who’s only good at destroying good things. He knows that Sam likes guys as well, he had seen him at school with the other kid.

Castiel doesn’t care about gender anyway. So… maybe Dean should set them up for a date. Maybe then his stupid heart would finally move on. Maybe Dean could move out, try to find himself a future husband and… and forget about those forbidden feelings.

Yes! This could actually work. Dean rubs over his chin.

How could he set them up though? His eyes wander over to the table to Sam’s laptop and he smirks. 

Oh _yes_.

  


*

  


“Come on Cas! This will be fun!” Dean says cheerfully while he tries to get the phone of the angel, who holds it away from him. Dean huffs.

“I do not understand why I would need a dating app.” Castiel answers almost snippy. Dean stops his movements to get the phone and then shrugs. 

He had spent all day yesterday on the damn laptop to find a dating app that would help him with his plan. He would make a profile with Castiel and then set Sam up with him. They’d write and fall in love and…

...and Dean will be free or something like that.

His heart doesn’t seem to get the idea yet.

“It will be fun! Come on, you’re going to meet other awesome people and can, you know… flirt and fall in love.” Dean says and Castiel sits down on his bed, Dean sits down next to him. The angel thinks about it for a moment.

“Normally Angels don’t fall in love.” Castiel says quietly but he smiles, while he strokes over his phone, this could be Dean’s chance.

“Just try it! I’m sure people will love you. Heck almost every waitress seems already gone for you just from your looks. And if it doesn’t work, then it wasn’t the right time. But you deserve some love.” Dean says, his smile hurts more than anything.

“Okay we can try it.” Castiel whispers and Dean takes his phone out of his hand. It doesn’t take him long so download the app to the angel’s phone and he opens it, ignoring how his fingers shake.

He… he wishes he could just lean over and kiss Castiel, tell him that he is the one who could give him the world but… he doesn’t. Not when he is also in love with his brother. Not when he doesn’t deserve either of them.

“So we need to give you a name first.” Dean says while thinking about something that wouldn’t be too obvious. He doesn’t want Sam to know it’s Castiel from the start. He hopes they can write anonymously first, fall in love and discover how perfect they are for each other. 

“I already have a name.”

Dean just has to smile at that.

“But you need a code name, just like when we’re pretending to be FBI.” Dean explains and already starts typing. He has to laugh at his idea, but it just fits Castiel so good. The angel shrugs.

“I don’t understand. If I’m going to date someone, shouldn’t they know my name?” Castiel wonders and Dean snorts.

“Obviously, but you don’t just give out your name to strangers on the internet. See it as a nickname, if you found someone and you talked for a while, you can tell them your name.” Dean explains and then shows the phone to Castiel.

“Sweetbee?” Castiel asks, surprised and Dean blushes under his gaze. Okay it might be a little too much and just as Dean wants to change it, Castiel smiles so cutely. Dean loves the gummy smile.

“I like that.” Castiel says and he looks down at the phone. The next minutes the spend together setting the profile up. Of course Castiel even chooses the bee icon and then they write down his characteristics.

“Of course I’m going to write you are grumpy in the morning, cause it’s true!” Dean laughs, when he hears Castiel grumble at that.

“You are grumpy yourself.” Castiel says, already crossing his arms and Dean chuckles sadly. 

“I know but I’m not setting up my profile here… It’s... I don’t think I’ll ever fall in love again, you know? Lost my big chance with Lisa long ago and it’s just not in my cards.” Dean whispers quietly.

He shouldn’t have started with that, because now Castiel looks sad himself. He puts his hand on Dean’s shoulder and squeezes. 

“Dean, I’m sure you will find someone.” Castiel tries, but Dean is already shaking his head. He gives the phone to Castiel and is already getting up. This is way too much and they finished setting it up anyway.

“It’s fine. Seriously I’m… I will be okay. I just want you to try it. You deserve it.” Dean says and he is out of the door, before Castiel can say anything. Dean leans against the wall and takes a deep breath. 

“Sammy!”

Sam is in the library again and Dean sits himself down on the plush armrest of the seat Sam is sitting on. Hmm, a book about witches. Not Dean’s favorite, he shudders and Sam looks up to him.

“You okay?” Sam asks and Dean nods before he can stop himself. If he would just scoot over a bit, he’d be sitting in Sam’s lap. It’s probably super comfortable and Dean craves it so bad, he -

“Uh, I wanted to show you something. Gimme your phone.” Dean says and to his own surprise, Sam actually gets his phone out of his pockets and gives it to Dean. Dean types the name of the dating app in the app store and waits for it to load.

“You will not download some porn on it again, will you?” Sam asks and Dean smirks a bit. Sadly Sam doesn’t even know half the truth. Sure Dean had used his laptop before to watch porn but more often enough it’s just a cover up.

On his own laptop he watches the gay porn he needs and doesn’t want anyone to see.

“Nah, but I’ll get you out to the world again, Sammy.” Dean says and he proudly shows the app to Sam, who groans.

“Dean, no come on, give it back.” Sam says but he only tries to get his phone halfheartedly. Dean chuckles and shakes his head.

“Come on Sammy! You know it’s been a long time since you had someone.” Dean says and winces inwardly, because that was kinda rude. He knows Sammy still misses Jess every day.

Sam rolls his eyes, but at least he doesn’t take his phone back.

“Fine, do what you want, I will just delete it later.” Sam mutters and Dean leans a bit against him, feeling his warmth through their flannels. The next minutes are quiet, Sam turning a page and Dean typing on his phone are the only noises.

Dean smiles while he writes everything about his brother down. He mentions his long hair and love for books. He still needs a profile pic and Dean browses for something that fits his brother the best.

He settles for some kind of dark flower and smiles. He’d easily fall in love with a guy like that. Well - he already did anyway.

“Done?” Sam asks, when Dean had stopped typing for quite some time. Dean nods and then holds the phone out for Sam to take.

“Just saying you should really try it. I know you don’t believe it, but you deserve your happy ending and all that.” Dean says, a bit embarrassed at such a chick-flick moment. Sam looks up at him and Dean gets up.

He needs some space between them.

Sam looks down at his phone and then laughs, when he sees his own profile. Dean swallows, but tries to laugh himself. He hopes he wasn’t too obvious.

“Really? Rapunzel?” Sam asks at the nickname and Dean blushes.

“Well you got the long hair, Samantha!” Dean mocks half heartedly but Sam is smiling brightly. Dean counts that as a win. Sam closes the app and then puts his phone down.

“This is really important to you, hm?” Sam asks and Dean nods. He won’t tell Sam the real reason of course, but he had meant it. Sam really deserves to be happy and Dean thinks Sam could be happy. With Cas.

“Yeah. Just… you know. Doesn’t hurt to try.” Dean says and he wets his lips. For a second he thinks Sam is looking at his lips, but he is for sure only imaging that. Sam nods slowly, lost in a thought.

“Okay. Maybe it’s not too bad.” Sam says and Dean nods again. He can’t believe his plan worked so well? He even searched for ‘Sweetbee’ and had added Castiel already to Sam’s friend list.

Now they could flirt all they want and realize that they are indeed perfect for each other. 

“See, thank me later!” Dean says and then he is already turning around and leaves his brother alone. He… he doesn’t want to see him fall in love with someone else. But he knows that will happen sooner or later anyway.

Right now though, he would need some pie and.. and then he would just watch a movie.

Alone.

He should get used to it, right?

  


*

  


Only a week later, Dean catches Cas and Sam on their phones all the fucking time. He doesn’t know what they write to each other, but they do smile a lot. 

He wishes he could be happy for them, but the jealous part in him grows bigger with each second. Even his fingers itch for something he shouldn’t touch.

Fuck, that was so not his plan.

“So huh. The dating app is good, yeah?” Dean tries when they eat dinner together. Castiel had excused himself earlier, so it’s just him and Sam.

His brother continues to type on his phone and only when Dean coughs slightly again, does he finally put it down. Dean waits for an answer.

“Yeah, I mean I never thought it would be a good idea, but I really came to like it.” Sam says and his smile looks real. Dean should be relieved, but it feels like something heavy grows around his heart.

“Oh, I mean, you found someone already?” Dean asks and he hastily puts some of his fries into his mouth, so he won’t let anything else slip. He wants to say so much more. 

“Yeah I think so. I… found someone. It’s… it’s a guy.” Sam says and he whispers the last word. Dean had already prepared for something like that. When they were younger, he hadn’t dared to talk to Sammy about topics like this.

But he had learned a lot the last few years. About himself as well.

“I’m happy for you.” Dean says and while his smile is a bit fake, it’s not because Sammy is online dating a guy. Sam seems surprised by that, but then he is smiling himself.

“Not a problem for you?” Sam still asks and Dean shakes his head. His smile gets a bit brighter.

“Nope. I mean there was a time when Dad was still around where I would’ve never want to talk about this but… yeah I’m my own person now. You’re fine, Sammy. Just be careful, like always.” Dean says and Sam looks relieved.

Dean doesn’t tell him he’s bi himself, there would be another time for that. Right now only Sammy matters. And his happiness.

“Wow. Yeah, he’s nice. I think I really like him.” Sam says, his smile growing softer with each word and Dean’s heart aches for something he can’t put into words.

After that Sam stops eating to text again, while Dean at least tries to focus back on his food. Maybe… maybe he should get the dating app himself. It wouldn’t hurt to find someone too, would it?

Sam snickers at the next text and Dean rolls his eyes.

“Hey uh… I’ll be in my room.” Sam says, not even taking his eyes off his phone and Dean nods. He doesn’t mind cleaning the dishes anyway. It would hopefully distract him from the fact that his brother will jerk off to the guy now.

“Yeah night.” Dean mutters, even though Sam is already out of the room. Dean clears the table and cleans the dishes, but somehow it doesn’t really help his thoughts.

Castiel didn’t talk to him a lot the last few days, always on his phone, but his smile looked so beautiful that Dean didn't want to destroy that. Sam isn’t ignoring him as much, but he is still reserved. 

Maybe it’s just the first honeymoon week or whatever. Love is always super exciting in the first week, it would calm down.

Dean shakes his head at himself and walks back to his own room when the kitchen is clean. He even packed some food away for Castiel. Sometimes he does like to eat Dean’s burger.

His own room looks cold and not cared for when Dean enters it. Sure he has his own personal things on his wardrobe and against his wall, but otherwise? Dean wishes he could share a room again with someone.

He never had this much privaty. When they were young, Dean always had to share a bed with Sam, because John would’ve never thrown some money away just for a second room. And after that he still shared motel rooms with Sam.

At the bunker, he’s alone. At first he had liked that, but now he misses someone next to him.

Dean sighs loudly and then dresses for the night. Just as he lays down on his bed, he takes his phone back into his hand. 

Should he really do this?

Maybe, yeah maybe he should just check out if Sam and Castiel are really still using the app or if they just pretend to get Dean to shut up about it. Dean nods to himself and then he had already downloaded the app.

He squirms when he opens the app, the layout already familiar and still it feels super different this time.

“Hmmm.” Dean makes, when he fills out his own profile. He can’t really put down hunting as a hobby, people will think it’s about deers or rabbits and Dean doesn’t particularly like that. He types in 80’s Rock, having a nice dinner and… romantic walks on the beach. Cuddling.

Sue him! He always wanted to try that. Besides nobody knows it’s him. He doesn’t have to pretend to be ‘oh so cool’.

Only his nickname is a problem. He has no idea. Everything with his Baby would be way too obvious and cheeky ones like “Pumpkin Pie” wouldn’t help either. Dean sighs.

Wait maybe he needs some half truth. Or a truth that nobody knows. 

_PrinceD._

Dean snickers at his own joke. It’s not super obvious or at least he hopes so. Dean remembers that as a kid he was always jealous of the princesses that got saved and didn’t have to do anything. Now he likes to save people, it’s not like anyone would want to save him.

(He still doesn’t get why Castiel saved him in the first place, or why Sam is staying.)

But he wouldn’t mind being carried on his hands either. And it matches Sam’s a bit. Even though Dean is sure in that relationship, he’d be the princess. Not that he would mind with Sam and Cas as his kings.

Okay wow. He should stop. That is not what he wanted at all.

He takes a pink heart as his profile picture, because nobody knows that he likes pink and finally saves his profile.

The app finally loads and Dean takes a deep breath. He searches for ‘SweetBee’ first and it actually shows up. Dean smiles and then matches him. To his surprise Cas matches him back immediately. 

Dean doesn’t know what to write to him, so he searches for his brother. It seems like Rapunzel is online as well and Dean takes a deep breath before sending out another match. Sam accepts it too and their chat opens, just like Castiel’s had.

Dean smiles and can’t help the warm feeling that spreads through his stomach. Fuck. They had both matched him.

He hastily throws the phone away when it beeps. He didn’t get the app to flirt with Cas or Sam. He just wanted to check on them.

He pulls his blanket over his face and sighs.

Fuck.

  


*

  


_> SweetBee: I wish I could hear your laugh. I bet it’s stunning.<_

Dean blushes badly and he even hides his face for a second. Oh yeah. Haha, it’s a funny story, so he was being a total coward and flirting with Castiel online. For almost a whole month and he can’t stop himself. 

Yeah he knows that he is an idiot, thank you.

_> PrinceD: I don’t know about that. My laugh is pretty loud.<_

Dean types back and he hates that he isn’t being able to let go. He still makes himself smaller than he is and he knows Castiel doesn’t like that. Never really did. Dean swallows. 

_> SweetBee: Oh I’m sure. I bet you are just as adorable as your messages are. You’re special and it breaks my heart that you can’t see it yourself.<_

Dean actually whimpers at that. Fuck. He wishes Castiel would tell him that to his face. Deam cuddles even more into his blanket and hastily types back. He knows it’s wrong but he can’t help it.

_> PrinceD: Stop that, you will make me fall in love with you.<_

Dean strokes over the display of his phone. That’s a clear lie. He is already in love with Castiel. He wishes he was brave enough to tell him, but he doesn’t dare to. He also feels bad that Castiel is so obviously flirting with him.

Maybe it means that it doesn’t work out with Sam.

_> SweetBee: Absolutely not. Maybe that is my goal?<_

Oh god. Dean’s finger twitch. While they had flirted a lot over the last days, it was never something so clear. Dean wants to send some emojis back, but he settles for something different.

_> PrinceD: Then you need to try harder ;) <_

Dean chuckles at the emojis he gets back this time. It’s already way after midnight and Dean knows they got a hunt the next day, but he can’t help it. He never had something like that.

Sure with Lisa it was love. But somehow this feels different. It feels hot and almost too much and Dean wants to drown in this feeling.

_> SweetBee: Fine. I’ll sleep for now and just dream about you in my arms.< _

Dean sends a heart back and closes his eyes. He bet it feels amazing to be in Castiel’s arms during the night. And if then Sam would press against him from behind it would be perfect. Dean feels himself smiling.

Just then his phone beeps again.

_> Rapunzel: Still online, so late?<_

Dean laughs. Yeah, shit. He isn’t only flirting with Castiel, like hell no, online he can flirt just as much with Sam as he likes. Nobody will have to know.

He just hopes Sam and Castiel don't ever speak about their online matches or they would both realize that he is flirting with them both. But lately they don’t seem to have grown any closer. Just like always.

_> PrinceD: Maybe I was waiting for you to show up.<_

Dean imagines Sam’s smile at that. Maybe Sam is laying in bed as well. Dean wishes they could share a blanket again, maybe he’d be allowed to put his head on Sam’s chest, just hearing his heartbeat.

Yeah he has it bad. He knows.

_> Rapunzel: I’d like that. I had a busy day, but I can promise you I was thinking all day about you. Imagining how it would feel to have you at my side.<_

Dean smiles, maybe Sammy is a mind reader sometimes. Dean aches for something like this and he has no idea how to ever stop this. Would he one day have to break Sam and Castiel’s hearts?

Dean shakes his head, he can’t think about that right now. He knows his own heart is breaking the whole time, but he’s too selfish to stop at the same time.

_> PrinceD: Yeah? You’re the cuddly type?<_

Dean hopes the answer is a yes. He never dared really to cuddle after sex. Most women knew he was only after a short fling and most of them liked that about him. Even when he dared to put an arm around of them, most weren’t too happy about it.

Some did cuddle back, but each time Dean had to be the big spoon. He wants to be the one wrapped in Sam and Castiel’s arms.

_> Rapunzel: Are you asking if I would cuddle you? Sure. I bet you would fit wonderfully in my arms. I’m rather tall.<_

Dean chuckles and for some reason he tears a bit up. He doesn’t let the tears fall though. Even crying alone in his room is kinda embarrassing. At least about something like that.

_> PrinceD: I never told that to anyone, but I would like to be cuddled and cherished. I never had that but I think it would be nice.< _

Dean grimaces at his own text, but it’s already too late, he had sent it. He can see that Sam is typing already and he hopes his brother wouldn’t judge. He knows Sammy is nice, but maybe he took it too far.

_> Rapunzel: I’d give you the world if you would let me. Prince I do really like you, I hope I made that clear in the last weeks. You are incredibly special.<_

Dean chokes on nothing and this time the tears do fall. He wishes he could tell him. He wishes even more that Sam would mean these words about him. Tell them to his face. 

He sends back a heart and then goes offline, before he does something stupid. He curls around his blanket and sniffles quietly.

“Please, please just once, let me have something good.” Dean whispers against his phone. He closes his eyes and pretends everything will be fine. That’s what he is best at.

  


*

  


“Hey.” Dean walks into the kitchen, but Sam and Castiel don’t even bother to look up. Dean nods to himself and then grabs himself some coffee. He can hear them both typing and sighs, when he feels his phone vibrate with new messages.

He knows he has to stop this.

“Dean I can’t thank you enough for this app.” Sam finally says and Dean’s head snaps towards him. They never really talked about it again and he has to be very careful now.

“Yeah no problem. You… still enjoying it?” Dean asks and Sam nods, before finally putting his phone away. Castiel smiles at Sam.

“You do seem happier, Sam. I hope he is treating you well.” Castiel says and Dean is a bit surprised that they seem to have talked about this before. The angel does know Sam is talking about a guy. Huh.

“I am. Really he’s just so nice and sweet, but I feel like he is not doing good. I wish I could sweep him up in my arms and make it better.” Sam explains and Dean sees that Castiel nods.

His face is in flames.

Sam had never said anything like that before. While Dean knows he did care about Jess or Sarah or Maison, he never heard Sammy talk about someone so tenderly. It feels good and Dean knows it shouldn’t.

“I have a similar problem with my mate. I told you about him before Sam. He’s shy and thinks he doesn’t deserve the endearments he receives from me.” Castiel explains and Dean has to turn around for a second.

Holy shit, he doesn’t know what’s worse. That Castiel called him _mate_ or that he told Sam that he is shy. Dean is not shy! Well at least not normally. This is different.

“Seems like you both got troubles with guys.” Dean finally mutters when he feels calm enough to look at Sam and Castiel again. Seems like Sam told Castiel that Dean doesn’t really care that he dates a guy. Or maybe the angel is just open like that.

“I think it’s good trouble. Some people are worth the effort.” Sam explains slowly and he even strokes over his phone, that is laying on the table. Castiel sits up more straight.

“I will do anything to make him understand how loved he is. I will show him that he deserves to be happy.” Castiel says and Dean has to swallow his coffee around the lump in his throat.

Shit he should’ve never started it. Maybe he can still stop this mess.

“Heh. Maybe you’re dating each other?” Dean asks and he is surprised when they both shake their heads. Dean frowns, why did his plan not work?

“I mean we found each other in the app, yeah. And we flirted a lot, right?” Sam snorts at that and Castiel puts his hand over Sam’s for a tiny moment. Dean’s chest roars in jealousy. And he doesn’t even know who he is jealous of. 

“We did and it’s nice, but I can’t get this other guy out of my head.” Castiel says quietly and Sam nods again. Dean feels himself nodding along. Seems like it’s not super strange to be in love with two people?

Dean had googled it a lot of the last weeks and there are a lot of people who are polyamorous and he likes those descriptions a lot. He still thought he would be kinda alone with that.

At least around his friends and family.

“Yeah same. I will just do anything to make him mine.” Sam says determined and Dean shudders under that voice. He loves it when Sam gets so rough like this. When his brother takes control. Just like Castiel does.

“Well then good luck I guess.” Dean mumbles and he hastily leaves the kitchen before his face gives too much away.

“We don’t need luck.” Castiel says, but Dean doesn’t even hear that anymore. He almost runs to his own room and he sighs, when he looks at his phone.

A dozen messages are waiting for him again and Dean sits down on his bed. Taking the time to read each one slowly. Castiel and Sam know exactly how to push his buttons. All his messages are sweet and romantic.

Dean feels himself blushing at the messages and he wishes he was brave enough to go back to the kitchen and tell them. 

But they would be angry. For one thing he lied at them, pretending to be someone else but they also could be angry that it’s _him_. He is not as perfect as he seems online. He’s a mess on a good day.

  


*

  


Two weeks later, Dean still didn’t do anything.

Well he did make it worse. He is still texting them both and he feels as if he falls in love with them more each day. Sure, he had known a lot about Sam and Castiel, they are his best friend and his brother.

But he had never known them like this.

“So, what is eating you?”

Dean looks up from his phone and sees Jody’s soft smile. He is out on a simple vampire hunt with her, while Sam and Castiel stayed back. Dean had insisted, to need some time alone. To his surprise it didn’t get to a fight.

It almost seemed as if Sam and Castiel were relieved to have the bunker on their own. Dean’s heart squeezes again, when he looks down to the cute message Sam just sent him. If they would know, they would be so angry.

“Nothing.” Dean mumbles, but if someone can detect his lies, it’s Jody. And this wasn’t even a good one. They’re at a lovely fast food restaurant and while Dean had ordered enough food for them both, he didn’t touch it so far.

Too deep in his thoughts and constantly on his phone.

“It’s it a girl?” Jody asks carefully while she eats her own pancakes. Dean ducks his head and he knows his ears turn red. He has no problem talking about this normally, but Jody is like… his mom.

“No…” Dean whispers, he knows Jody won’t judge it, if he likes guys. But still. She can never know about it being Sammy and Castiel. He should’ve kept his mouth shut. Dean hastily bites in his burger, getting sauce all over his fingers.

“It’s fine. You know that I’m here for you no matter what. So tell me about this guy.” Jody says and she holds out her napkin. Dean grimaces, but he takes it. He’s glad she didn’t clean his mess up for him. He chuckles.

“He’s cool. I mean… I really like him, but there are a couple problems. You know how it is.” Dean explains and moves on to his fries. He finally realizes how hungry he actually is. Jody tilts her head.

“I do not know. I mean yeah Love is never easy, but you gotta fight for it.” Jody says and Dean nods. He gets this squirmy feeling in his stomach again.

“I lied to him.” Dean says and shrugs.

“And? You lie to people all the time. I mean… how do you tell someone you’re a hunter? I’m glad Donna knows our lifestyle.” Jody says and Dean shrugs at that. He’s actually sad Donna is not here with them, but ‘babysits’ the girls.

“Ah not about that really. I uh… I know him and then pretend to be someone else on the internet and now he’s flirting with me, but doesn’t know it’s me?” Dean says and Jody looks at him. She takes the newspaper next to him, rolls it up and smacks it softly on his head.

“You’re an idiot, sweetheart. I mean why don’t you tell him? If he likes you online, he for sure likes you in real life as well. I mean you are a real catch, hm? You got the biggest heart I’ve ever seen.” Jody says and she takes Dean’s hand in hers. She squeezes it and Dean can feel those stupid tears welling up in his eyes again.

“I can’t risk it.” Dean mutters and then he takes a deep breath.

“What if… what if, I’m… can you be in love with more than one person?” Dean whispers, afraid someone else will hear them and also that he makes a fool of himself. While he read about it online, he is sure some people judge lifestyles like that. Even though there is nothing wrong with it.

“Of course you can. That's why you’re afraid, you think you can’t have both?” Jody asks and Dean nods again. He’s glad Jody is like always so understanding.

“Yeah I mean… isn’t it unfair?” Dean asks and in his head he is still imaging that Sam and Castiel fall in love, too. That would feel better to Dean somehow, even though he knows both are possible.

“Not if you tell them before someone gets hurt. I know you hate talking about your feelings, but I think the boys will be happy to have you.” Jody says and Dean blushes again, before he groans.

“Okay enough chick flick talk. Tell me about the girls? And can I have another milkshake?” Dean says and Jody laughs. Dean feels more happy anyway. Like someone lifted a huge weight from his chest.

A few hours later, Jody pays and they both separate at the parking lot. The vampires are already taken care of, they killed them before breakfast already. Dean hugs Jody as hard as he can. Still determined to come clean with Sam and Castiel.

“Take care, you hear me boy? And call when you get home.” Jody says and Dean chuckles. God, he has missed this. Jody is really like a mom to him and he can’t say how much he needed this in his life.

“I will. Probably gonna crash here in a motel room though and drive back tomorrow.” Dean says and Jody nods, before she actually fixes the collar of his jacket.

“Good.” Jody presses a short kiss to his cheek and then hops into her truck. Dean smiles, when she rolls the window back down.

“And I hope it works out with Sam and Castiel.” Jody says and before he can answer anything else, she is already driving away. Dean gasps at nothing for at least 5 minutes before he gets into his own car.

What the fuck.

He is sweating all the way to the motel he had seen earlier. Jody knows. Fuck. Okay, she hadn’t killed him and she didn’t seem angry but Dean feels worse anyway. 

Dean gets himself a room and falls on his bed. He should calm down a bit and he can’t help but smile, when he sees that he got a few new messages. He opens Sammy’s first.

_> Rapunzel: I hope your work meeting went well, I miss you when you don’t write me.< _

God, why does he have to be so cute and romantic? Dean’s heart beats a bit faster, when he sees that Sam even sent a picture. That never happened before. His fingers shake when he opens it, but he has to smile.

It basically shows that Sam is laying on his bed, fingers curled around the pillow that is next to him. Dean wishes he could really fall asleep on the spot next to Sam. While he had always problems with sleeping (or with waking up every hour at night), he had always slept peacefully with Sam at his side.

_> Rapunzel: Here would be the perfect space for you.< _

Dean can’t help but flirt back. He is already so addicted to all their pet names, the implied romantic things and the nice words. It feels as if slowly his soul heals from years of torture. 

_> PrinceD: Yeah and then what would you do to me?<_

Dean doesn’t really know what he expects, but he switches back to the chat with Castiel. Only to see that Castiel had sent him a picture of some flowers. They look gorgeous and Dean thinks they are from their tiny garden.

Castiel always sends him cute pictures of his day and Dean had even done so himself a few times, nothing major, but he hadn’t known how much fun that could be.

_> HoneyBee: I plucked those today and I wish I could give them to you. They’d look so lovely in your arms.< _

Dean squirms a bit on his bed. He would be so spoiled by those two, he can’t believe it. He sends Castiel some hearts first and then replies properly.

_> PrinceD: I bet I would look even better in your arms.<_

Castiel is fast to answer. 

_> HoneyBee: Oh I’m sure of that. Sadly I do have some work to do myself today, but I can’t wait to catch up with you tomorrow, beloved.<_

Dean wipes over his face. Dammit, there is no way he deserves someone as affectionate as Castiel is. He sends a message back and then relaxes against the bed. It somehow feels like cheating too now.

Castiel doesn’t know he is flirting with Sam and the other way around. He shakes his head and decides to take a cold shower before he would sleep. Ten minutes later he feels a bit better, tomorrow.

Tomorrow he would tell them. He has to.

Maybe then they would never speak to him again for various reasons, but they don’t deserve this, they deserve so much more.

Just as he’s laid down, his phone beeps again. It can’t be Castiel, but it’s Sam who answers and Dean’s eyes widen at that message. Because this is also new.

_> Rapunzel: I’d fuck you into my mattress.<_

Holy shit. Dean can’t help this full body shudder and his heart beats a lot faster too while his blood wanders downside. Sure in his darkest hours, he had thought of this, but he would never dared to start it.

Dean bites on his lip. Shit okay. Forgotten are his plans to tell them tomorrow.

_> PrinceD: I have to say that I would really like that. You gonna be a gentleman?<_

Dean had known since he was sixteen that he liked guys just as much as girls. He remembers exactly how he had liked one of his classmates. So far he never acted on any crushes on men before.

Too scared to get caught and even when John died, he felt bad, because he knew he had always wanted Sam. And then Castiel too.

_> Rapunzel: I would make it real nice for you. Lay you out on my bed, kiss you until you’re breathless and then I’d carefully kiss down your neck. Maybe behind your ear?<_

Dean feels already breathless and he groans quietly. Luckily he’s just in his boxer shorts after the shower and he carefully strokes his hand over his stomach.

_> PrinceD: Definitely behind my ear. I’d be so good for you.<_

While Dean never had a male sexual partner, he had soon realized that he likes to be the submissive partner and he hopes that is what Castiel and Sam would like him to be as well.

Dean chuckles to himself, when he sees how fast Sammy is typing.

Someone is eager.

_> Rapunzel: You better be good, doll. I would kiss down your neck. Carefully, slowly and maybe I tease your nipples a bit, watch them get hard under my care.<_

Dean groans when the message ends there. He wants to know more. Instead he uses his free hand and strokes over his own nipple. He loves the feeling and moans quietly. He can’t even remember the last time he was alone. 

_> PrinceD: Fuck yes. Tell me more. Would you ruin me?<_

Hmm. Well Dean never had sex online too. Normally he would show a person what he likes and try out what gets them off. He’s a pleaser more than a taker, but this feels good too, even if Dean doesn’t really know what he is doing.

This time, Dean gets another picture. His eyes almost fall out, when he sees that Sam had thrown his blanket away and his hard dick strains against the black boxer shorts he is wearing. 

Dean can’t see enough, but oh he can imagine. Fuck.

_> Rapunzel: You make me so hard, baby. I want to cherish you slowly. I’d bite your thighs, cover your stomach in kisses and if you’re real good, I would open you up with my mouth first.<_

Dean doesn’t know what’s worse. The picture or the message.

_> PrinceD: You have no idea how much I want this. Please, it’s not enough!<_

Dean’s fingers slowly wander down to his dick and he pulls his own underwear down. His dick is already perking up against his stomach and Dean strokes his cock a few times. This feels so good. 

_> Rapunzel: Such an eager baby, huh? I would take my fingers to help open you up. Pump them in and out, until you’re screaming for more. I want you to beg for me. And do it nicely.<_

Fuck. This is torture!

Dean hastily turns to the side so he can lean over the bed and grab his bag. He finds his lube and sighs. Thank god, he always has that with him. He pours some over his hand and then strokes himself again.

He’s fully hard just from that and Sammy’s dirty words.

>PrinceD: Please, Please! I will be so good, I promise. I will do everything you want. Wanna feel you inside, please?<

Dean doesn’t care that he is actually begging. He strokes a bit faster but has to stop, because he already feels close to coming. 

_> Rapunzel: Good boy, of course. I would be careful, let you get adjusted to my size and once you have, I’d fuck you for real. Make you sit on my lap, take my cock so good, baby. Come on, stroke yourself.<_

Dean chokes on nothing, he can’t help but imagine to sit on Sam’s huge cock. Fuck this is straight from one of his fantasies.

_> PrinceD: Feels so good, you’re so big.<_

Dean is lost in his fantasy and strokes himself faster. He has no idea how he can still hold onto his phone, but he has to. He wants to read it all. 

_> Rapunzel: Yeah? You like it when I split you open. Oh I’d be so good to you, help you stroking your own cock, I want to see you come on my chest so bad.<_

Fuck, it’s so hot in this room. Dean moans louder and louder. He doesn’t even think about annoying his neighbors, not that he cares at all.

_> PrinceD: Close.<_

He doesn’t have the strength for more.

_> Rapunzel: So good, doll. Then come for me, scream my name and make a mess all over us.<_

“Holy shit, Sammy.” Dean groans, when he comes over his own fist. He thinks he even blacks out for a few moments. That was intense and in the end it was just his own hands and well maybe Sammy’s dirty mouth.

He hadn’t known Sam was this dominant and hot during sex but he’s happy that he could have this once. His phone beeps again and Dean tears up when Sam writes he came just as hard.

So much for telling them. He would just have to delete this app and never mention it again, as much as it will hurt them. Dean sniffles. And himself, too.

He would… do it slowly.

  


*

  


Days later, Dean is at home and he still has the app on his phone. He was less online though and it had already hurt both Castiel and Sam. They wrote a dozen messages why he had been ghosting them.

Dean made excuses but continued with his behavior.

It’s night again and he has received over twenty messages in the last hour. Dean can hear his phone vibrating with each one, while he tries to focus on his book. His eyes always wander back to his phone.

He finally takes it.

_> HoneyBee: I miss you so much. Did I do something wrong?<_

Dean squeezes his eyes shut and for a moment he wants to throw his phone against the wall. With his luck Castiel and Sam would hear that and storm inside his room to demand what happened.

_> PrinceD: No but I told you, it’s me. You deserve someone better, I’m sorry.<_

Fuck, he should’ve never started this stupid idea in the first place. He looks to the end of his bed, he has a duffel packed. He had thought about leaving and he is still not sure if he should, but he can’t stay here either and pretend things are fine.

_> HoneyBee: That is not true, you are the best human I’ve ever met.< _

Dean chokes on his laughter, because yeah only Castiel would write something like that. He doesn’t really know what to write back, just as Sam sends a text. Of course.

_> Rapunzel: Baby, did I hurt you somehow? I can’t sleep without our texts anymore.<_

Just as bad as Castiel’s message. Fuck, he is hurting them so badly and he knew that it would end like this. Well okay, he hadn’t known they would actually like him back. He was sure he’d be the only one with a broken heart.

Dean was never… was never one who people liked for being just him. They liked that he saved their asses, maybe liked his face or his dumb jokes. 

But… Castiel and Sam had always known him more, of course. That’s normal since they are his brother and best friend. But in this little online chat, Dean had opened up more than he ever had.

He had told them about his hidden panties, about his insecurities, about his liking towards soft touches and cute dates, he’d never been taken to. About his nightmares and even about how he had always… longed for love.

Dean wipes over his right eye and then writes Sam back.

_> PrinceD: You were perfect, I’m sorry. I just can’t do this anymore. I really… I really hope you find someone who will be worthy for you.<_

Dean can’t help the tears now. He would write them that this ends now and then he will delete this stupid app, get his stuff and leave. Maybe he can find a nice beach.

He goes back to Castiel’s chat, when he sees there is a new message. It’s a voice message and Dean’s heart stops. He just _has_ to listen to that. He opens it and his heart stops when he hears the rustling starting.

“I meant what I said, you make my world better with each day. I wake up with a smile when I think about you, I hope I can spend the rest of our lives with you together.”

The messages end there again and Dean hiccups for a moment. For a short moment he wonders, if he can save that somehow, so he can hear it over and over again, while he licks his wounds.

Just then Castiel sends another one.

“I love you.”

Oh.

Dean squeezes his eyes shut but it doesn’t help to keep the tears in. They fall down his cheeks and Dean doesn’t make another attempt to wipe them away. He waited years for this. For words like that.

But he doesn’t deserve them.

His app shows a new message from Sam and Dean can’t help but click on that. It’s also a voice message and Dean believes this is a joke.

“Hey Sweetheart. I just… I miss you so much and I hope you miss me too sometimes. You are the sweetest person, I’ve ever met and I… I don’t think I can go on without you.” 

Dean sees another voice message. He clicks it. Just to hurt himself more.

“I love you, baby.” 

This time he cries loudly in his hands. He doesn’t deserve this. His lies got him something like that, but he would never have this in real life. 

It was better when he didn’t know how it was to be loved back. Now it would just sting each day of his life. 

He hastily shuts his phone off and throws it under the bed. He would leave it here, so his brother and the angel can’t track him down. He only pulls his robe over his shirt and sweatpants with the hot dogs on and gets his bag.

He could dress properly later, far away, he doesn’t care. He needs to leave now!

Dean struggles a moment with his boots and he knows he looks so ridiculous like this, but it’s not like anyone will see him. He takes another look at his room and then nods to himself.

He just has to tell himself that it’s better this way. Sam and Castiel deserve better. He would text them from a burner phone the truth and he can just pray that they would move on from this mess.

Please, let them be okay. 

He doesn’t really care about himself anymore. Dean wipes over his face and then walks over to the door. He looks back at his room and gasps when he runs into something very solid. Dean swallows.

He looks up in Sam’s angry eyes.

“Uh huh.” Dean mumbles and when he looks behind Sam and sees Castiel also standing there. It would be funny, if Dean could laugh right now.

Castiel is wearing a blue robe himself, that Dean had never seen before, his chest is naked and his legs are also not clothed. Dean swallows. Sam wears dark pajama pants and a white shirt. 

“What do you think you’re doing?” Sam asks and he actually raises one eyebrow. Dean almost shrinks down at that, even though he never backed down before. But now he knows Sam’s dominant side first hand. 

“I was just… getting out for a short drive?” Dean tries but even he knows what a stupid excuse that is. Why would he do that in his robe anyway? And where would he drive. Out to watch the stars?

Huh, he should actually do that somet-

“Bullshit.”

Dean has to say he is surprised to hear Castiel talking like that. He had never heard the angel swearing before. He wishes he could say that he doesn’t like it.

“Dean.” Sam says so sternly that Dean crumbles under the gazes. He stumbles back into his room and sits down on his bed, and tries to hide his tears from them. He sniffles anyway and apparently they heard that.

“Hey no, Dean you’re fine.” Castiel says hastily and before Dean can do anything his brother kneels in front of him, taking Dean’s hands in his own. Dean lets the tears fall quietly, but he has his eyes closed.

The bed next to him dips and then he feels another hand curling around his shoulder. Dean wishes the ground would swallow him up.

“Dean hey, don’t cry sweetheart.” Sam whispers now and Dean wishes he could stop crying, but it’s hard. He gets one hand out of Sam’s and wipes over his face. Trying to clear his thoughts.

What should he tell them?

“I made a huge mistake a-and I need to fix it.” Dean finally whispers and he looks at the door again. He was so close, he doesn’t even know why Sam and Castiel were in his room. 

“What mistake?” Castiel asks carefully. His hand is now stroking over Dean’s back and it feels nice, but Dean knows he shouldn’t relax into that touch. 

Dean wants to show them their messages on his phone, but he doesn’t want to embarrass one of them in front of the other like that. Besides, his phone is still under his bed. 

“I… I uh I messed with you and.. I’m sorry, I never meant for it to escalate like this and I swear I never wanted to lie to you and all I said to you wasn’t even a lie and now you.. now I … I…” Dean doesn’t even understand himself, but for some stupid reason Sam is smiling.

Dean looks over to Castiel who has a soft smile on his lips, too. He doesn’t understand.

“Dean I want to show you something.” Sam says and then he gets up himself. His knees crack loudly and normally Dean would joke about that, but he is too scared now. Sam gets his phone out and Dean swallows way too loudly.

“Yeah there is something you should know.” Castiel whispers and when did he get so close? Dean looks how Sam opens the dating app on his phone and then with a few clicks, he shows that there are two people he wrote messages to.

HoneyBee and PrinceD.

“So this one is Cas, as you know, since I have the feeling you kinda wanted us to meet on this app, otherwise why would you install it on both our phones on the same day?” Sam explains slowly. 

Dean doesn’t move.

“And this one is the other guy I fell in love with. He is really sweet, super adorable and showed me something I needed all my life.” Sam explains slowly and he points to the pink heart Dean had used as a profile.

He knows he is blushing, but seems like his body betrays him today like he wants.

“Cas?” Sam says and when Dean looks over to Castiel, he sees him holding his phone as well.

“I got Sam right here too but also the same cute and wonderful guy under him. I’m in love with him, but that’s actually no surprise.” Castiel whispers and he carefully strokes over his display.

Dean wants to run away, but it seems like they wait for an answer.

“Uhm, that’s… a funny coincidence.” Dean whispers and Sam rolls his eyes but he is smiling. Castiel snorts.

“Okay look here. I read a bit into the app when you first installed it and I talked to Cas right after it. See the app is pretty nice and all but it has one small function, you should’ve read into, before you made your own account.” Sam says and he holds up his phone.

There are the terms and conditions - and who reads that shit - but Sam is pointing at a certain sentence. Dean’s eyes widen at that.

“See the app works only if there are some people one mile around you. Only then you can message them. Since we’re alone at the bunker…” Castiel starts and Dean knows by now even his ears are bright red.

“You both knew it was me the whole time.” Dean finishes lamely. Shit. 

“Yeah. Luckily once you send a message to your match you could continue even if you were far apart, otherwise I wouldn’t have had the wonderful night a few days ago.” Sam says and Dean gapes at nothing.

“What Sam wants to say, Dean, why… why do you think we wouldn’t love you? I’ve been in love with you for almost ten years.” Castiel continues and Dean looks back to him. He slowly gets up from the bed and looks at those two.

It’s kind of a shock. Even if it’s a good one.

“And I’m in love with you for almost my whole life.” Sam says and Dean’s eyes snap back to him. He isn’t sure that this is really happening, but his hands are shaking badly by now. He takes a deep breath.

“I’m a bit overwhelmed.” Dean stutters and they both laugh at him.

“And to take your next worry. We both know that you flirted with the two of us the whole time as well. And we came together a few weeks ago and we would really like you to be part of that relationship.” Castiel says slowly. 

Dean blinks once and then again. 

“Yes.”

He can’t even say more because before he can take another breath, Sam is already with him and presses him against the doorway to kiss him. Dean closes his eyes and finally relaxes. Sam kisses him slowly and with so much care, Dean whines against his lips.

He can feel that Castiel is holding his hand and he doesn’t think he has ever been happier. All this stress for nothing. Dean chuckles and he really is breathless from Sam’s kiss. Just as Sam breaks it, Castiel is already kissing him as well.

Dean is sure that he never felt more happiness than in this moment. 

“Never do something like this again, okay?” Sam says and he presses his forehead against Dean’s. Dean nods, he would never do something stupid like this again. He doesn’t want to lose Castiel or Sam ever again.

“I’m really sorry. I was scared, I thought you would hate me. I’m… I’m your brother and Castiel is an angel.” Dean tries to explain and he means it. Castiel strokes over his cheek, smiling so softly.

“It’s okay Dean. You didn’t hurt us, we meant every word we wrote to you. And we also know that you still need to accept how much we love you. That you are worth the whole world. And so much more.” Castiel says and Dean leans against him. 

He already loves their hands on him.

“I meant every word I said as well. Really I… I’m happy.” Dean says and he gets another two short kisses. If you ask him, they should never stop kissing ever again. 

“Good, because we won’t ever let you go again. But it’s way after midnight and I’m super tired.” Sam says and he walks over to Dean’s bed. Before anyone can say something he cuddles under the blanket.

“Come on.” Castiel says and he takes Dean’s hand to get him over to the bed as well. Dean is a bit confused but sits down on the bed. Castiel kneels down and helps him out of his boots, while Sam pulls his robe down. 

Dean feels so loved.

“I bet you’re exhausted too, huh?” Sam laughs, when Dean crawls under the blanket as well. Dean nods and then dares to cuddle against Sam’s chest. It feels like he imagined. Castiel fits himself behind Dean.

It’s a very tight fit but somehow they make it work. Dean feels incredibly hot, but never has he been this safe. He closes his eyes and smiles, when Castiel’s arms come around him to hold Sam’s hand. Dean squeezed in their middle.

“I’m in love with you too. Uhm both.” Dean whispers and he can hear their twin laughter, before they hug him from both sides. 

“We know.” Sam whispers and Dean punches his chest.

Idiots. All three of them.

**Author's Note:**

> I hope you liked it!
> 
> Find me on [tumblr](https://notfunnydean.tumblr.com)
> 
> If you are interested. I have my very own Discord family! You can totally join us. We're a funny group and RP as SPN characters, go crazy about the show and just have a lot of fun! If you do wanna join - check out [my page](https://notfunnydean.tumblr.com/post/626183144788410368/spn-discord-family) about it.


End file.
